


Through It All

by Sams_Princess



Category: Supernatural
Genre: Adult Baby Dean Winchester, Age Play Caregiver Castiel (Supernatural), Age Play Little Dean Winchester, Baby Dean Winchester, Caregiver, Daddy Castiel, Day Care, Diapers, Emotions, Gen, Headspaces, Little's are known, Littles, M/M, Non-Sexual Age Play, Pacifiers, Soothers, bottles, kind off
Language: English
Status: Completed
Published: 2020-11-22
Updated: 2020-11-22
Packaged: 2021-03-09 20:35:51
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,188
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27672133
Author URL: https://archiveofourown.org/users/Sams_Princess/pseuds/Sams_Princess
Summary: “Look,” Charlie exhaled softly. “I think we’re going to be okay. He’s sleeping right now; hopefully for another hour or so at least – he needs it after all that crying he’s done. And for all we know he could wake up as right as rain with his usual charming Dean smile and that contagious giggle we all long to hear.”“God, I hope so,” Cas mumbled. “Will you call me if he doesn’t?”“Of course!”“And I’ll drop everything here and come and pick him up. I think it’s safe to say that a certain baby just needs his Daddy.”It was only 40 minutes later (and half hour into his next meeting) that Castiel got another phone call from the Day Care. This time it was Anna and she sounded almost frantic.“Dean’s woke up from his nap,” She informed him seriously, voice rushed. “But he woke up Big.”
Relationships: Castiel & Dean Winchester
Comments: 12
Kudos: 179





	Through It All

**Author's Note:**

> So I should be writing Picture This, What We Are, Patience and Trust Me to name a few. But this idea came to me and I couldn't stop my fingers from typing it out!!  
> It was supposed to be a cute little story about Cas dropping Dean off at Day Care and Dean getting up to mischief while there; but this happened instead. It wasn't even supposed to be written from Cas' POV. But sometimes, I guess that's just the way the cookie crumbles and you gotta go where your muse takes you. And this is where my muse took me.  
> I hope you enjoy it!!

Dean grumbled from behind his soother as soon as the familiar building came into view. Cas flicked his eyes to the rear-view mirror for a fraction of a second, not surprised to see a pout on his babe’s face. He refocused his attention back on the road just as quickly, knocking the indicator on and pausing to wait for a space in traffic so he could safely turn into _“Busy-Bee’s Day Care Centre”_.

“No Daddy,” The Little in the back seat whined. Cas rolled his eyes at the grumpy boy, as he tapped his finger on the steering wheel, still watching for his gap in the commuting traffic. He huffed impatiently, thinking about the long day ahead of him and wondering just why Dean had chosen today to wake up on the wrong side of the bed.

“No?” He asked the babe softly, taking the gifted opening to drive into the carpark of the Day Care, putting his hand up in silent thanks to the Ford driver who had held back so that Cas could turn in without waiting any longer. “No to what, Jellybean?”

“No Bee’s!” Dean wailed, his tone suggesting that his Daddy should have already known what he meant.

“You don’t want to go to Day Care?” Cas asked in surprise as he put the car in reverse and began to carefully guide the car into the nearest parking space. “I thought you loved coming to Busy-Bee’s, hey?”

“No!” Dean snapped, throwing his head back against the headrest of his car seat dramatically. His feet kicked out and caught the back of the passenger seat.

“Hey, come now,” Cas soothed, his voice slightly harder as he checked the wing mirrors to ensure he was within the parking lines. “There’s no need to kick the car, is there?”

“No!” Dean bit, voice sharp and frustrated.

Cas rolled his eyes at the irritable Little again, knowing that the ‘no’ was a disagreement, rather than the agreement he’d been looking for. He chose not to reply to the boy this time, because it wouldn’t get them anywhere. Whether Dean liked it or not, he was attending Day Care today.

When Cas deemed his parking good enough, he turned the car off, unclipped his seat belt and climbed out of the car.

“Wanna go home, Daddy!” The babe complained when Cas pulled the car door open.

“I want to go home too, Sweetheart,” Cas muttered kindly, reaching over the boy to release him from the five-point harness. He slipped his hands under Dean’s arms and hoisted him out of the car and pulled him to rest against his hip. “But Daddy has some boring grown up stuff to do today and so Dean has to go to Busy-Bee’s and have lots of fun with all his friends, okay?”

“No,” Dean sobbed, snaking his arms around Cas’ neck and tucking his head into the man’s shoulder. “Wanna go home Daddy!”

“Oh Jellybean,” Cas cooed, reaching into the footwell of the backseat, pulling out the grey diaper bag and resting it on his shoulder. “You’re going to have lots of fun today. And Daddy will be back to pick you up before you know it.”

Cas dipped into the front pocket of the diaper bag and pulled out a spare soother. He offered it to his surly babe who took it rather eagerly, but still continued to pout from behind it. Cas felt his heart swell with love for the boy who was just too darn cute for his own good and pressed a kind kiss to his temple.

Once Cas had the car locked up, he crossed the carpark to enter the building. There to greet him was Kevin, Busy-Bee’s Day Care’s receptionist.

“Good morning, Dean,” Kevin greeted cheerfully, pausing his furious typing to paint a huge smile on his face for them both and welcome them into the Day Care. “Good Morning, Mr Winchester.”

“Good morning Kevin,” Cas nodded at him with a friendly smile. “You gonna say hi, Jellybean?”

Dean shook his head defiantly and tucked his face further into Cas’ shoulder, trying desperately to not let the receptionist see his face.

“Sorry Kevin,” Cas apologised to the younger man. “He’s not a happy boy this morning.”

Kevin spent a few small moment’s trying to get a smile from the Little, but wasn’t successful. He quickly gave up.

“Oh dear,” Kevin hummed. “We really aren’t happy this morning, are we?”

“I’m afraid not,” Cas hummed, a gentle hand cupping the back of his boy’s hair, gently massaging his scalp just the way he knew the babe liked. He felt rather than heard Dean’s pleasant hum at the gently fingers.

“I’ll buzz you through,” Kevin informed them, reaching over to the relevant button. “Perhaps Anna will have better luck than me at getting a smile, hey?”

“Thanks Kevin,” Cas smiled again, pulling on the internally locked door when he heard the familiar click that told him it was open.

Dean didn’t attend Day Care as often as some of the Little’s Cas knew. Cas was lucky enough to be self-employed and therefore be able to work around Dean and his needs. But there were some days, such as when he had a deadline fast approaching, that Cas just knew the babe was going to get under his feet; or days where he had meetings and events that Dean couldn’t attend. Normally, Dean loved his sessions at Busy-Bee’s and there were day’s where he’d get a sulk on or throw a tantrum when Cas had to tell him he wasn’t going; so the Daddy made sure to sporadically book his boy in every so often just for the hell of it. So, although Dean wasn’t a regular at the Day Care, he certainly wasn’t a stranger to it.

With this in mind, walking the corridors of the colourful room wasn’t something Castiel, or Dean were new to. But the way Dean clutched his Caregiver tighter, trying to push himself further into the man’s embrace, the way he sobbed into his shoulder and uttered a mantra of _“No Daddy”_ from behind his soother, that was all new.

“Come on, sweet boy,” Cas hushed, pausing outside the “Bay-Bee’s” room to take a minute to try and sooth his clearly distressed boy. “Daddy’s _got_ to go to work today, baby. If he could cancel his meeting and take you home, then he would. Daddy will try and come back as quickly as possible. You’ll have your nap, and then afternoon snack and just before tea time Daddy will be here to pick you up. Does that sound okay, Jellybean?”

Dean shook his head and choked out a sob.

“I’m sorry, Dean,” Cas cooed, feeling like the biggest asshole in the world as he reached out and pushed open the door of the Bay-Bee’s room.

The room was large and colourful, with lots of soft furnishings and things at floor level so the Little’s that chose not to walk could still get to everything with ease. The room was warm and inviting and the quiet nursery rhymes playing out of the speakers gave the space a peaceful vibe. Anna and Charlie, two of the usual Bay-Bee’s staff were wearing huge smiles as they engaged with the four little’s already in their care.

The little bell above the door tingled as Cas entered, grabbing everyone’s attention. Anna, the Bay-Bee’s room manager, bounced up from the floor and rushed to greet them with the biggest smile on her face.

“Good morning!” She cooed, reaching her fingers out to tickle lightly at Dean’s side. Dean, who normally soaked up any and all attention that Anna gave him (because, Cas suspected that his babe had a little-boy crush on her), shied away from her touch with a wail of protest, once again trying to push himself further into his Daddy. “Oh no! What’s the matter Sugarplum?”

“We woke up on the wrong side of the bed, I think,” Cas supplied for him, shrugging the diaper bag off his shoulder and reaching over to place it on the coat peg that had a smiling picture of Dean above it. “So, I’m afraid I’m dropping off a very grumpy boy this morning.”

“Oh, it’s no big deal. I’ve dealt with many a grumpy-babe in my time, Castiel,” She chuckled, opening the register for the Daddy to sign his baby in. “I’m sure we’ll be able to get a smile out of him before you know it!”

Castiel’s eyes flicked to the clock on the wall, located Dean’s name in the register and jotted down the time and his own initials next to it.

“I’m sure he’ll be okay soon enough,” Castiel agreed, putting the pen down and returning his hand to Dean’s head. “If I could, I’d take him home – but this appointment I’ve got today is ridiculously important.”

“Don’t you worry about it,” Anna dismissed friendly with a wave of her hand. “I have no doubt that Dean will be his usual happy, smiley self when you pick him up!”

“I hope so,” Castiel sighed. He looked at the time again and cringed; he should have been on the road 10 minutes ago. If he didn’t leave now he’d be late. “Right,” He announced, giving Dean a slight warning before he started to loosen his hold on the Little.

“No!” Dean cried loudly, the tears falling down his face thick and fast now. Castiel smiled at him sadly and just decided to rip it off like a band-aid.

“Daddy will be back later, Dean. You have lots of fun today, okay?” He kissed his forehead and then started leaning towards Anna who took the hint and put her hands under Dean’s arm so she could take him from his Daddy. “I love you lot’s, Jellybean.”

Dean was screaming now, arms held out towards Cas in wordless request. It took everything in Cas not to take him back and go home.

“Call me if you need _anything_ ,” Castiel told Anna above his baby’s crying.

“He’ll be okay, Castiel,” Anna reiterated again. “Come on, hunny – say goodbye to Daddy.”

Castiel bid another quick farewell and ducked out of the room.

Dean’s crying got louder as soon as Cas was gone, and the sound of his baby’s distress followed him back through the corridors and back to the reception area.

Kevin, who could also hear the Little’s cries smiled at him sadly as he passed.

“I’ll get them to give you a ring as soon as he settles,” Kevin offered kindly. “I’m sure it won’t be long.”

Cas muttered his thanks and darted out the building and back to the car.

~THROUGH IT ALL~

Cas had just managed to make it to his meeting on time. He tried to submerge himself in his work, but he’d be a liar if he said his thoughts never strayed to the bawling Little he’d left at Day Care earlier that morning.

Halfway through the first meeting, Cas had taken a phone call from Kevin who tried to tell him in the nicest way possible that Dean still wasn’t settled.

“He’s calmed some,” The receptionist had tried to reassure. “But he’s still having a few wobbly moments.”

Cas knew that was Kevin not wanting to let the worried Caregiver know that his Little was still distraught. Still, he thanked the Neutral on the other end of the line and asked him to give him another ring if they needed to.

When Castiel managed to sneak away for some lunch, he phoned through to the Day Care and asked Kevin if he could speak to Anna or Charlie. Kevin patched him through, and it was Charlie that answered.

“How is he?” Cas asked, holding a hopeful breath – he could hear happy babbling in the background instead of the heart-wrenching cry he’d been expecting.

“He’s sleeping currently,” Charlie admitted sadly. Cas closed his eyes – it was an hour earlier than normal, but he had no doubt that he’d have done the same if Dean had been like that at home. Dean probably needed it. “Had about 20 minutes so far.”

“I bet he didn’t go down easy,” Cas huffed, almost cringing at the thought of it.

“Oh no,” Charlie chuckled kindly. “No Sir. We tried everything and in the end, we got desperate and called Jack in.”

Cas whistled low; Dean loved his Uncle Jack and was probably the closest he was to another Caregiver after Cas. Jack was Cas’ younger brother and had been besotted with Dean as much as Dean had been besotted with him. Jack worked at the Day Care, but he worked in the Bumble-Bee Room which cared for Little’s that were a lot older than Dean’s usual mindset, so they didn’t get to see each other often when Dean was there. If they’d called Jack out of his Room for help, things must have been truly dire.

“How was he with Jack?”

“It worked a little I guess,” Cas could hear Charlie’s shrug through her tone. “I think because Jack looks so much like you. And he reached out to Jack; he actually wanted Jack to hold him. But he still didn’t settle. It took half an hour of rocking, pacing, and singing from Jack before Dean finally fell asleep.”

“Thank God for Jack, eh?” Cas half-joked. The smile in his tone, however, didn’t show on his face.

“You’re telling me. Dean just,” Charlie sighed. “Well, he hasn’t had a great morning in all honesty. He hasn’t eaten anything either and he’s refused every bottle – even the one Jack tried to offer him. And every time we’ve managed to check his diaper, he’s been dry.”

“Do you need me to come and get him?” Cas muttered into the phone, knowing how well that would go over with his agent, but knowing without a doubt that Dean was way more important than any of this. It was clear something really wasn’t right with Dean and it wasn’t just him being stubborn at this point.

“Look,” Charlie exhaled softly. “I think we’re going to be okay. He’s sleeping right now; hopefully for another hour or so at least – he needs it after all that crying he’s done. And for all we know he could wake up as right as rain with his usual charming Dean smile and that contagious giggle we all long to hear.”

“God, I hope so,” Cas mumbled. “Will you call me if he doesn’t?”

“Of course!”

“And I’ll drop everything her and come and pick him up. I think it’s safe to say that a certain baby just needs his Daddy.”

It was only 40 minutes later (and half hour into his next meeting) that Castiel got another phone call from the Day Care. This time it was Anna and she sounded almost frantic.

“Dean’s woke up from his nap,” She informed him seriously, voice rushed. “But he woke up Big.”

“Shit!” Cas cursed, squeezing his eyes shut and pinching the bridge of his nose. That really wasn’t good. Dean was apart of the 0.4% of the Little population that was classed as being a High-Level Little. That meant that Dean needed to be regressed near all the time. Being ‘big’ for any prolonged length of time could be detrimental to both Dean’s physical and mental health.

And of course, with Cas being 26 miles away, Dean couldn’t have picked a worse time to de-regress.

“I’m on my way.”

~THROUGH IT ALL~

When Cas arrived, Kevin barely stopped to greet him. The receptionist no doubt knew what was happening and knew how important it was for Cas to get to Dean right now. Cas rushed through the internal door, his long coat flaring behind him as he paced it down the corridor towards the Bay-Bee’s room at record speed.

“I’m here,” Cas announced as he entered, voice laced with worry. He didn’t have time for pleasantries, he needed to see his baby. The panic that was flowing through him right now was enough to put him on edge and he needed Dean right now, as much as Dean needed him. “Where is he?”

“He’s through here,” Charlie informed him, flying to her feet upon his appearance. She led him quickly across the large room towards another door that Cas knew led through to the cosy sleep room which was lined with cribs. “Jacks been with him this whole time – but I don’t think it’s helped none.”

Cas said nothing, taking a moment to glance through the window in the door. He could see Jack crouched in front of Dean who was sat in the rocking chair. Cas could tell just from looking at Dean that he was Big – and he didn’t look happy. His arms were crossed, and he had the sourest look on his face as Jack spoke to him.

“Take as long as you need,” Charlie offered, before moving away - back to the other Little’s who needed her care and attention right now.

Cas took a deep breath before pushing open the door and slipping into the sleep room. The sound of the door caught the inhabitant’s attention, and both turned to see just who was disturbing them.

As soon as they realised it was their knight in shining armour, he was greeted with almost identical looks of relief.

“Cas,” Jack sighed, his shoulders dropping. Cas didn’t think he’d ever seen his younger brother happier to see him.

“Daddy!” Dean cried at the same time, bouncing out of the rocking chair, and flinging himself into Cas’ arms.

Before Cas could even try and lift Dean onto his hip, Dean was all but climbing the man, his legs wrapping around Cas’ waist and his arms latching around his neck. He was suddenly sobbing loudly, his face buried in his Caregiver’s neck.

“You left me, Daddy!” Dean wailed, his hands clutching fists of Cas’ coat.

Cas knew that the ‘Daddy’ Dean kept using wasn’t a sign that the Little had instantly slipped back into his headspace upon sight of him. No, it was just what Dean had always called him.

When Cas had first taken Dean in, Dean had been so against his headspace that Cas had put a multitude of things in place to try and help Dean regress and accept that he was a Little and not the Neutral a certain John Winchester had forced him to be. One of those things had been that Dean had to call him ‘Daddy’, always. If the Little ever called him anything else, Cas would have ignored him until he was addressed properly. It hadn’t taken long for Dean to realise what Cas was doing, but it had taken much longer for Dean to accept it and for the Daddies to start rolling naturally of the tongue. Dean had become so used to calling him ‘Daddy’ when he was both Big _and_ Little that he’d once admitted it just didn’t feel right calling him anything else, in either headspace.

“It’s okay; Daddy’s here now. Daddy’s got you. God; I’m sorry, Dean. Daddy’s so sorry,” Cas uttered, feeling like the worlds biggest failure right now. Dean had been upset this morning because he had been right on the edge – he’d been so close to slipping out of his Little headspace that all he’d needed was his Daddy to help him. And Cas hadn’t noticed! It was his job to notice!

“Stop it Cas,” Jack spoke up, voice hard, recognising the anguish on his brother’s face. He might not have his own Little just yet, but Jack seemed to be able to read Cas’ thoughts. “Maybe Dean _was_ close to de-regressing this morning, but you weren’t the only one who didn’t realise that’s what was happening. No one did, Cas.”

“I should have known though,” Cas admitted, completely downtrodden as he gently swayed the boy in his arms. He felt close to tears himself, took a shuddery breath and pressed a gentle kiss to Dean’s temple.

“But Dean didn’t show any of his usual signs,” Jack argued with him. Cas closed his eyes and repeated that to himself. Because it was true; Dean hadn’t show _any_ of his usual signs of de-regressing – apart from his clinginess to Cas which wasn’t overly unusual at the best of times.

“I should have just left work when I spoke to Charlie earlier.”

“Stop beating yourself up over it Castiel,” Jack ordered, his Daddy-tone accidentally slipping into place. “You’re here now – and that’s what matters!”

“You’re right,” Cas muttered, nodded his head. “I’m here now, eh Jellybean?”

Dean nodded with a sniff and unashamedly wiped his runny nose on Cas’ coat. Cas chose not to say anything about that and instead refocused on his babe.

“Dean, sweetheart,” He cooed. “Do you know why your Big right now?”

Sometimes, Dean just knew why he de-regressed, which was always beneficial because then Cas could help the Little work through it faster so that he could return safely to being Little.

“Just am, Daddy,” Dean yawned, rubbing at his wet, tired eyes.

And other times, Dean just didn’t have a clue why.

It wasn’t actually unusual for High-Level Little’s to slip out of their headspaces. And depending on the Little it might even be considered healthy to do so from time to time. But, Dean was probably as High-Level as they came (and Cas was pretty sure some of that was down to the upbringing his boy had had); and being Big for any prolonged amount of time really was just asking for trouble.

“That’s okay, baby,” Cas reassured him, taking the few steps across the room to lower himself into the rocking chair and hold his boy close. But with Dean now sitting in his lap, he could feel that his boy was missing something vital.

“Dean,” He started, voice a little harder now as he pushed Dean back slightly so that he could see his face. He fixed the Little with a knowing look. “Are you wearing your diaper?”

Dean muttered something and shied away slightly, clearly knowing he was about to be reprimanded. The diaper had been another thing Cas had been strict on right from the start. Little’s in his care wore a diaper at all times, even if they were big – especially if they were prone to accidents as frequently as Dean was.

Cas raised his eyebrow at Dean, and Dean ducked his head.

“No Daddy,” He whispered. Cas hummed.

“What does Daddy say about Little boys and their diapers?”

“Little bums should always be padded,” Dean recited with a whine. He opened his mouth to continue, but Cas cut across him.

“So, why aren’t you wearing yours, Little boy?”

Dean’s cheeks immediately heated and he groaned at the blatant reminder at his secondary gender.

“I…” Dean glanced over his shoulder at Jack, who just raised his eyebrows at him in the same was his Daddy did.

“Go on,” Jack encouraged, although his Daddy-voice was still present. “Tell him what you did.”

“Dean,” Cast pressed, his tone suggesting Dean had reached his boundaries.

“I… I threw it,” Dean confessed shyly, trying to tuck himself back into his Caregivers chest and ignore the way Cas’ eyes bled with disappointment.

“You threw it?”

Dean’s bottom lip slipped out and began to wobble and the boy’s eyes started to gloss over with new tears. It was a wonder Dean still had any tears left to cry at this point and Castiel made a mental note to make sure his boy got plenty of bottles to ensure he stayed hydrated.

“I took it off and threw it…” Dean paused to take in a shaky breath. Castiel waited him out, wanting to know what he was going to say. “I threw it at Jack-Jack.”

For a moment, Cas was speechless. He hadn’t expected that. Sure, they had had tantrums like this when Dean had been new to this; Dean’s favourite past time used to be throwing things. But he was usually so good now, even when he did get all the confusing Big Dean thoughts.

Cas glanced over at his brother for confirmation, who pointed out the clearly wet diaper which was just under the window.

“I am very disappointed Dean.”

Dean whined, hating the sad tone his Daddy’s voice took on.

“I don’t imagine being in a wet diaper was very nice. But neither was throwing it, Dean Winchester. How do you think Jack-Jack felt?”

Dean said nothing for a moment, unable to look the Caregiver in the eye. He pulled on the bottom of his top anxiously.

“Sad?” He guessed, sounding Little.

“I think so. What should you have done instead of throwing a tantrum, huh?”

“Change it.”

“Excuse me?” Cas asked, not happy with that answer. And Dean knew why. He wasn’t allowed to change his own diapers.

“Asked Jack-Jack to change it.”

“Good boy, that’s right,” Cas nodded, moving to stand again. He hadn’t expected to be moving again so soon; he’d wanted to take a few quiet moments with his babe, gently rocking the chair to hopefully lull Dean back off to sleep. “Jack, you couldn’t grab me his diaper bag, could you?”

“Course,” Jack nodded, slipping out the room almost silently.

Dean whined, knowing what was coming.

“What’s the matter, huh?” Cas asked, rearranging Dean in his hold until the Little was sanctioned comfortably on his hip. “We need to get a clean diaper on you before you have any little-boy accidents, right?”

Jack appeared before Dean could reply. Cas quietly thanked his brother as he accepted the grey bag and flipped it open with one hand while his other kept a firm, strong hold on his currently reluctant babe.

As Cas laid out the foldaway changing mat, humming quietly to Dean as he went, Jack moved over to the window. He silently gathered up the wet diaper from the ground and placed it in a diaper sack. He left the room again to dispose of it in the appropriate bin.

While he did that, Cas shushed his whiny babe as he lowered him onto the changing mat.

“Daddy,” Dean complained, trying to sit back up again as soon as he was out of his Caregiver’s arms. He suddenly sounded Big, without a single hit of his Little headspace in sight.

“No,” Cas scolded, Daddy-voice in full force, pushing Dean gently back down again with a firm hand on his stomach. “You know the rule, Dean. Remind me of it again, Sweetheart.”

“Little bums should always be padded,” Dean seethed, crossing his arms.

“And yours isn’t, is it, Little boy?”

“No.”

“Sorry?”

Dean closed his eyes and was clearly trying to get a rein on his frustration and, most likely the humiliation that was burning through him at the moment – even though they were the only ones in the room right now.

Cas was not oblivious to the fact that even though only moments ago Dean had been regressed, even if ever so slightly, now he was nothing but pure Big Dean. Which, Cas fretted, was worse; Dean was supposed to be going further into his regression – not leaving it.

Cas also understood that seeing his Caregiver after spending the day longing for him was what had pushed Dean into his headspace, however slight it was. But the headspace hadn’t been deep enough; and evidently, the prospect of having his bottom diapered had pulled Big Dean firmly back into place. The diapers had always been something his boy had struggled with, despite so obviously needing them.

“No. _Daddy_ ,” Dean hissed, a heavy dosing of sarcasm lacing his tone.

A moment later, the Little cried out, his eyes snapping open at the pain that was suddenly blossoming on his inner thigh.

“Daddy!” He protested; voice now outraged as he reached for his thigh in hopes to rub out some of the sting from the slap.

“Daddy isn’t going to put up with any sassiness, Dean Winchester,” Cas informed him, as the door opened again, and Jack came back in. Dean’s face heated upon the sight of his ‘Uncle’ and, in an attempt to hide, he threw his arms over his face.

“Good boy,” Cas hushed when Dean made no further objections. He kept a gentle hand on Dean’s tummy, to enforce that he wasn’t going anywhere, as he pulled out everything he needed for the change. With speed and practiced precision, Dean’s elasticated jeans were removed (of course, with no access to any underwear – his boy was naked underneath) and his knees were pressed up to his chest as Cas slid the fresh diaper underneath him. After a quick wipe, some cream to ward off any potential rashes and a healthy sprinkling of baby powder, Dean was soon expertly taped securely into a fresh diaper.

“There we are,” Cas declared cheerfully with a gentle pat on the front of his boy’s diaper. He didn’t replace Dean’s trousers and instead reached down to take Dean’s hands away from his face so he could pull the babe into a sitting position.

“Daddy is _not_ happy that you threw your diaper at Jack-Jack,” Castiel said. Dean didn’t even look sorry, the displeasure of being subjected to his Daddy’s stern voice evident on his face, his arms crossing across his chest portraying his feelings further. “I will not have you throwing _anything_ at _anyone_. Do you understand Little boy?”

The fire in Dean’s eye flickered as he glared at the Caregiver before him. Cas could play the Little at his own game and refused to be the one to break eye contact. He raised his eyebrow, in a silent warning that Dean knew only too well and wasn’t surprised when the Little ducked his head with a huff.

“Yes, Daddy,” He grumbled quietly.

“Good. Now, I want you to go and apologise to your Uncle Jack for throwing your diaper at him and then you’re to park your freshly padded bottom in the corner for 15 minutes,” When Dean didn’t immediately move, Cas spoke up again, his voice sharper. “Now, Dean.”

Dean scrambled up and shuffled over to Jack. He muttered some half-assed apology to the other Caregiver, which Jack accepted with a small chuckle and then was sent to the corner with a pat to his diapered bottom.

“15 minutes start now, Dean,” Cas informed him once the Little had taken his place.

Dean shuffled on his feet, but said nothing – which was the only way a chastised Little was expected to behave when he was in the corner.

With Dean’s back now turned, Cas let his shoulders sag. He let out a frustrated sigh and pinched the bridge of his nose in thought. He really needed to get Dean regressed again, and quickly. However, he had a feeling that the Little wasn’t going to go down easy this time.

“Hey,” Jack whispered as he crouched down in front of his kneeling brother. “You okay?”

Cas let his eyes flicker over to the man in the corner and after a moment or two of thought nodded slowly.

“I will be,” He promised quietly with a small smile. He grabbed Dean’s jeans and started folding them. “Thank you for sitting with him, and I’m sorry about the diaper thrown at you.”

“It missed me by miles,” Jack dismissed with a chuckle, clearly finding the memory funny. “And you know I don’t mind watching him; but boy I always forget how much more stubborn Big Dean is.”

“And that’s saying something,” Cas scoffed, packing the now folded jeans away in the diaper bag. His boy could go without them for an hour or so, it wouldn’t harm him. “Because we all know how stubborn Little Dean can be.”

“Daddy,” Dean whined from the corner, clearly not liking the kind discussion the two Caregiver’s were having about him.

“15 minutes starts over, Little boy,” Cas reeled off immediately, not surprised to have to do this.

Dean hated corner time, always had, no matter which of his headspaces he was in. It had taken a lot of time and effort to drum into the boy the rules he had to follow when he had his nose in a corner. Cas fondly remembered one time, right at the beginning, when Dean had climbed out of his crib by himself. He’d placed the Little in the corner for 10 minutes – but it took Dean almost 3 and a half hours to complete those 10 minutes because of his continued, blatant disobedience.

“But…”

“Let’s make it 20 minutes,” Cas decided calm as anything. “We can keep adding minutes if you want to keep talking Dean. You are in the corner; you _will_ stay silent or you will be there a very long time.”

Dean grumbled his complaint with a stamp of his foot (oblivious to how Little that one action made his look) but rightfully remained silent. Normally, Cas would have added another 5 minutes to the boy’s sentence or made him start over for that – but he let it go, figuring that he really ought to get Dean home sooner rather than later.

Once he was sure that Dean wasn’t going to protest any further, he nodded once and stood up.

“Look,” Jack sighed sadly. “I’ve gotta get back to work. I finish at 4 tonight – I’ll give you a ring later and see how you’re getting on?”

“That would be great,” Cas smiled, pulling his brother in for a brief hug. “I’m sorry we had to disturb your workday with this.”

“Don’t be silly Cas,” Jack shook his head. “Family comes first – always. I’ll catch you later.”

Once the bubbly, puppy-eyed man that was Cas’ younger brother had left, a soft, comfortable silence fell on the room.

Cas sat back in the rocking chair and waited patiently until Dean’s 20 minutes were up, the soft sniffing coming from the boy breaking Cas’ heart.

“Time’s up, Dean,” He spoke quietly, careful not to make the Little jump. “Come here, Sweetheart.”

Dean left the corner eagerly and clambered into his Caregiver’s lap. Cas accepted him readily, holding the boy close to him again, wiping away the wetness around his eyes.

“Oh, Jellybean; don’t cry.”

“I’m sorry, Daddy,” Dean sobbed before he was overtaken by a big yawn. Cas pressed his lips to the boy’s forehead, overcome with love for how cute his boy was.

“You’re forgiven, my boy,” Cas assured, his voice soft. “Please don’t do it again.”

“I won’t, Daddy.”

Cas rocked them in the chair for a couple of minutes, enjoying the feeling of his baby in his arms, before deciding that they had probably outstayed their welcome at the Day Care.

“Daddy?” Dean asked, confused when Cas stood and maneuvered him into a better hold. He looked around blearily and Cas realised that Dean had been dozing.

“It’s okay Jellybean,” Cas shushed, guiding Dean’s head back to his shoulder. “It’s time for us to go home now.”

Cas slung the diaper bag onto his shoulder and moved to leave the sleep room.

“My pants!” Dean cried, as if suddenly realising that he was still missing them. He struggled slightly in his Daddy’s hold, but Cas was an expert in holding Dean’s wriggly bum.

“Your pants are in the bag, Dean,” Cas told him, not stopping as he pulled the door open. “You’ll be fine Sweetheart. It’s not cold out and we’ll be in the car before you know it.”

Dean groaned but didn’t complain any further than that – knowing that there was no chance he was going to win this battle. It wasn’t that he was worried about getting cold – it was more about everyone seeing him and his very clearly diapered bottom. He hid his face in Cas’ neck, not wanting to face anyone in his current mindset.

The playroom was cooler than Dean had expected after having spent so long in the sleep room. He shuddered and curled up further into his Daddy, recognising the feeling of being on the edge of his Little space.

“How are we?”

“Well, we’re not quite regressed again yet,” Cas replied to Anna, his hand back on Dean’s head. Dean hummed at the touch. “But I don’t think we’re far off.”

“Oh, Sugar,” Anna said, reaching her hand out to gently pat Dean’s exposed thigh. “You’ve had a rotten day, huh? I think you just need to head home and have cuddles with your Daddy on the couch, yeah?”

“That’s the plan, isn’t it, Jellybean,” Cas muttered against his temple, sealing his words with a kiss. Within minutes, Cas had thanked the two ladies in the room, apologised for the trouble both himself and Dean had put them through and bid them goodbye.

On the way out of the building, Cas stopped at the reception and cancelled Dean’s session for tomorrow.

“Even if he is back in his headspace by tomorrow, I won’t be going to work,” Cas informed Kevin. “We’ll just have a nice, relaxed Daddy and Dean day, I think.”

And before Dean knew it, he was being placed in his car seat.

“Daddy,” He said, pushing the man’s hands away, really struggling with his headspace right now. He was teetering right on the edge and just wanted to give in, but for some reason he just couldn’t.

“Come on Jellybean,” Cas shushed, not fazed by Dean’s struggles as he successfully pulled Dean’s arms through the straps and buckled him in. “You know you have to travel in your car seat. If you don’t, you could get hurt – and Daddy would get into a lot of trouble, huh?”

Dean whined, and Cas brushed his hair back making a mental note to book him an appointment at the hairdressers soon.

Next, Cas placed the diaper bag in the footwell below Dean and paused to pull out another soother. This one was attached to a string, decorated with the word ‘Jellybean’ spelt out in colourful square beads.

“Here we go, Sweetheart,” Cas hushed, holding out the soother.

For a moment, Dean eyed it wearily, clearly undergoing an internal battle. Cas was just starting to think that the Little wouldn’t accept it, that he’d have another disagreement on his hands, when Dean reached forward and gently took the large plastic nipple in his mouth.

“There’s my good boy,” Cas praised, a huge smile on his face. He bestowed a kiss to his baby’s face and quickly clipped the other end of the string to Dean’s clothes.

Cas dived one more time into the diaper bag and pulled out a completely different item this time.

“Taggy!” Dean called out, voice lisped around his soother, when he recognised the item. It was Dean’s comfort item – a taggy blanket; coincidentally named ‘taggy’ by the boy himself.

Cas chuckled at his sudden enthusiasm and handed the boy the blanket.

“Come on sweetheart, let’s go home.”

~THROUGH IT ALL~

Dean was lightly dozing by the time they reached home, only 20 minutes later. Cas wanted to get Dean into the house and upstairs in his crib without waking him, and was confident that he could do so. Dean, however, came to as soon as Cas pulled open the car door and started unclipping him from his car seat.

“Daddy?” Dean yawned, the soother falling from his lips.

“Hi, Jellybean,” Cas shushed – not giving up hopes that his boy was going to sleep again. He needed a good, long nap, god damn it; and Cas was going to see that he had it.

“We home?”

“You bet,” Cas hummed as he gathered the Little, the diaper bag and the bag he’d taken to his meetings and trundled them all into the house.

“I’m not Little, Daddy,” Dean admitted, still half asleep when Cas pushed the door shut with his foot and dropped the two bags to the floor. Dean spoke as if he was only just suddenly coming to this realisation.

“I know, Sweetheart,” Cas shushed him, pleased that Dean had thought to admit that to him. Admitting it was something Cas had tried to instil in Dean since the very beginning of their relationship. It was the one area the babe still struggled with – but Cas blamed Dean’s upbringing for that. “But that’s okay. Daddy’s here, and Daddy’s going to help you. Okay?”

Dean yawned and nodded.

God, Cas couldn’t help but turn to mush. Dean was his whole world, his everything. He loved his boy with every fibre of his being. And he wanted to do so well by him.

“You need a nap, my boy,” Cas spoke, doing so more to fill the silence of the house than anything else.

“Already had one,” Dean informed him, barely lifting his head from his Daddy’s shoulder. He was still half-asleep, but there was an air of determination around him – he didn’t want to sleep. “At Bee’s. Ask Jack-Jack.”

“I know,” Cas said as he pulled a ready-made bottle from the fridge and fired up the bottle warmer. He was surprised when Dean didn’t complain just at the sight of it. “I know you had a nap at Day Care, Jellybean. But it’s been a day and a half for both of us, and Daddy say’s you need another one.”

“But Daddy,” Dean fussed, starting to really wake up now. It had been a good, long while since Cas had insisted on him taking two naps a day. “I don’t need another nap. I’m not Little at all, let alone _that_ Little.”

“Daddy knows that, Dean,” Cas said, voice still soft but with an underlying firmness to it. “But you know that being Big isn’t good for you, Sweetheart. Sometimes, a nap can help us reset the batteries and allow you to slip back into your headspace. Not only that, but Daddy can see he’s got a tired baby – and he knows that a cranky Dean gets into trouble. I don’t want to have to keep sending you to the corner baby, and I doubt you want that even less, huh?”

Dean said nothing, but his resident pout had returned.

“Come now, Daddy’s feeling sleepy too. We’ll go up to the big bed and we can cuddle. How does that sound?”

Dean seemed to think about it for a moment, before he nodded.

“Sounds nice, Daddy.”

“I thought so too, Jellybean.”

Once the bottle was warmed through enough, Cas took it with them as they ascended the stairs. He dipped into the nursery to quickly change Dean’s wet diaper and to put him into a footed baby grow (much to the Little’s disgust) before he let them both into his own room.

He let Dean sit back against the pillows, his soother back in place now as Cas had taken it from his t-shirt and reattached it to his sleepwear. Cas quickly undressed, leaving himself in only his boxers before he climbed into the bed and bundled Dean into his arms.

“Come here, my sweet boy,” Cas cooed.

“I feel rubbish,” Dean complained when Cas gently pulled the soother from him with a wet pop. “I honestly feel so crap right now, Daddy.”

“I know, Dean-Bean, I know,” Cas shushed, moving the boy gently so that he was comfortably cradling him. In the short space of time that Cas had been with Dean this afternoon, the boy’s mood had changed multiple times, and drastically. It was only to be expected with a High-Level Little like Dean. The poor thing _really_ needed to go back into his headspace, and soon – otherwise he was going to make himself poorly. “It’s because you’ve been Big for too long, Baby.”

“But I don’t want to be Big anymore,” Dean sniffed, his eyes suddenly overspilling. Tears started to flood down his cheeks. Cas’ heart broke at the sight and he bundled the boy closer. He pulled the comforter around them to keep the chill of the room away. Dean turned his face into Cas’ chest, his closed fist coming to rest just above his Caregiver’s pec. “I don’t want to be Big anymore, Daddy!”

“Hey, hey,” Cas shushed, brushing his hand down the Little’s face. “It’s all going to be okay, Dean. Daddy’s here; you’re not alone hunny.”

“I can’t get Little, Daddy,” Dean wailed, clearly distraught. “I can’t! What if I stay Big forever? I don’t want to be Big forever!”

It wasn’t the first time that Dean had voiced that very fear, but he had only admitted it very few times, and often when he was at his most vulnerable. Cas was always overcome with a ridiculous amount of pride whenever Dean ever confessed this. Once upon a time, Dean’s biggest fear had been actually _being_ Little. But with Cas’ love, time and determination, he had come to accept who he was. Now, Dean clearly preferred and relished in his Little side.

“Come now, Dean,” Cas spoke, voice lined with his Daddy-voice, knowing that it’s what Dean needed right now. “You’re the most beautiful boy, Sweetheart, and Daddy loves you _always_ – even when you’re Big. But Daddy’s here to help you, and that’s just what I’ll do. Daddy will never stop helping you, Jellybean, because Daddy loves you so much.”

Dean didn’t reply. He just continued to cry loudly into Cas’ chest. Cas let him cry himself out, proving soft words and kind touches as he saw his babe through this meltdown. It took a couple of minutes, but Dean started to calm himself down.

“There we go, hey?” Cas muttered, pressing a soft kiss to the boy’s forehead. “Do you feel any better?”

Dean’s eyes welled up again and he shook his head.

“Oh, Sweetheart.”

Cas left the bottle on the nightstand, knowing without checking that it was cold by now. He shuffled down the bed and wasn’t surprised when Dean moved from his arms and plastered himself up against his Daddy.

“Come on baby,” Cas whispered, wrapping his arms around the Little and pulling him closer. “Close your eyes. We’ll both have a little snooze, and hopefully you’ll feel much better when we wake, yeah?”

Dean hiccup, wiped at his eyes with the sleeve of his baby-grow and then nodded.

To help Dean relax, and to hopefully send him into a peaceful sleep, Cas started singing. In less than two minutes, Dean was asleep, his little puffs of air brushing against the skin of Cas’ chest.

“Daddy loves you so much, Dean,” Cas promised, another kiss to the boy’s head before he too slipped off to visit his dreams.

When he next woke, it was to a wriggly boy against him.

“Dean,” Cas grumbled into his pillow, a bit grumpy at being woken. “Daddy’s sleeping.”

“But Daddy,” Dean mumbled, clambering all over his Caregiver. “I’m hungry!”

Cas couldn’t help but smile, popping open one eye to take in the boy before him. The nap had clearly worked, Dean was once again submerged deep in his headspace. He both looked and sounded a lot better. Cas make a quick decision that a bit of enforced regression over the next day or two would help Dean stay rooted in his Little side for a good while.

“But Dean,” Cas groaned, copying Dean’s tone, over dramatically. “I’m tired!”

Dean stifled a laugh at his Daddy’s behaviour before he climbed off the bed.

“I want cookies,” Dean informed Cas, clearly determined to get his food.

Cas wasn’t going to deny him something to eat, remembering that his boy hadn’t had anything since breakfast this morning (which seemed like a million years ago) and clambered out of bed after him.

Dean squealed in delight as he was scooped unexpectedly into the air. He burst into fits of giggles; his head thrown back completely carefree; just how Cas always aimed for him to be.

“I don’t know about cookies,” Cas told him as he settled him on his hip. “But I’m sure we can find something to feed that greedy tummy of yours.”

And he took Dean down to the kitchen, settled him into his highchair and set about making scrambled eggs for his boy, all the while basking in the sight of Dean’s huge smile and the sound of his magical giggles.

When Dean had finished eating, Cas took him into the living room and set him down to play. But the babe didn’t want that. He clambered onto the couch and cuddled into his Daddy and quietly watched Thomas the Tank Engine, sucking on his soother and drowning out the sound of Daddy making call’s and apologising to multiple people for cancelling the meeting’s he had, had that afternoon.

When Cas finally put the phone down, Dean glanced up at him with a soft smile and spoke with a slight lisp around his soother.

“I love you, Daddy.”

Cas’ eyes lit up and a huge smile fell over his face. There really was nothing else that Cas loved more than being Daddy to this little boy. Dean was his everything. It might have taken them a little while to get to where they were now, but Cas would go through it all again in a heartbeat. Because Dean was worth it.

“I love you too, Jellybean!”

**Author's Note:**

> I might write a part two to this yet, because I would love to see a Daddy and Dean day!!  
> Also, got so much of a backstory for this that if you're all interested I might look at writing it up!! Let me know!!  
> Hope you're all well!! <3 <3


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